Regioselectivity of reductive debromination of substituted pentabromobenzenes with sodium tert-butoxide in DMSO

Russian Chemical Bulletin

Volumn 54, Issue 10, 2005, Pages 2379-2383

  Shishkin, V N ^a   Tarasova, I V ^a   Butin, K P ^b  

^a OGAREV MORDOVIA STATE UNIVERSITY   (Russian Federation)

^b MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

Reductive debromination; Regioselectivity; Substituted pentabromobenzenes

Indexed keywords

EID: 33645521392     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11172-006-0126-1     Document Type: Article

References (33)

1. V. N. Shishkin and K. P. Butin, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1990, 84
2. [Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, 1990 (Engl. Transl.)].
3. G. Beck, E. Degener, and H. Heitzer, Justus Liebigs Ann. Chem., 1968, 716, 47.
4. T. Linden, Recl Trav. Chim. Pays-Bas, 1951, 49, 781.
5. I. Collins and H. Suschitzky, J. Chem. Soc. C, 1969, 2337.
6. V. N. Shishkin, K. K. Lapin, B. S. Tanaseichuk, and K. P. Butin, Zh. Org. Khim., 1990, 26, 2181
7. [J. Org. Chem. USSR, 1990, 26, 1882 (Engl. Transl.)].
8. J. F. Bunnett and R. R. Victor, J. Am. Chem. Soc., 1968, 90, 810.
9. N. S. Zefirov, in Mekhanizmy geteroliticheskikh reaktsii [Mechanisms of Heterolytic Reactions], Nauka, Moscow, 1976, 113 (in Russian);
10. N. S. Zefirov and D. I. Machon'kov, Chem. Rev., 1982, 82, 615.
11. G. E. Hall, R. Piccolini, and J. D. Roberts, J. Am. Chem. Soc., 1955, 77, 4540.
12. J. F. Bunnett and C. C. Wamser, J. Am. Chem. Soc., 1967, 89, 6712.
13. D. A. Evans and D. J. Baillargeon, Tetrahedron Lett., 1978, 3319.
14. K. P. Butin, A. A. Ivkina, V. N. Shishkin, and O. A. Reutov, Vestn. Mosk. Univ., Ser. 2: Khim., 1983, 24, 382
15. [Bull. Moscow Univ., Div. Chem., 1983, 24 (Engl. Transl.)].
16. V. N. Shishkin, B. S. Tanaseichuk K. K. Lapin, A. A. Ivkina, and K. P. Butin, Zh. Org. Khim., 1984, 20, 2588
17. [J. Org. Chem. USSR, 1984, 20, 2357 (Engl. Transl.)].
18. H. Furujama and S. Fukushi, J. Synth. Org. Chem. Jpn, 1971, 29, 413.
19. W. Qwist and H. Wikman, Acta Acad. Ab., Math. Phys., 1959, 1.
20. M. P. Doyle, M. A. Van Lente, R. Mowat, and W. F. Fobare, J. Org. Chem., 1980, 45, 2570.
21. H. Furujama and J. Fudzi, J. Synth. Org. Chem. Jpn, 1971, 29, 92.
22. D. J. Berry and B. J. Wakefield, J. Chem. Soc. C, 1969, 2342.
23. G. F. Hennion and J. G. Andersen, J. Am. Chem. Soc., 1946, 68, 424.
24. N. N. Vorozhtsov, G. G. Yakobson, and N. I. Krizhechkovskaya, Zh. Obshch. Khim., 1961, 31, 1674
25. [J. Gen. Chem. USSR, 1961, 31 (Engl. Transl.)].
26. W. I. Awad and A. I. Hashem, Egypt. J. Chem., 1973, 16, 269.
27. V. N. Shishkin, I. Yu. Bolusheva, K. K. Lapin, and B. S. Tanaseichuk, Zh. Org. Khim., 1991, 27, 1486
28. [J. Org. Chem. USSR, 1991, 27, 1303 (Engl. Transl.)].
29. USSR Inventor's Certificate 1 606 508; Byull. Izobret., 1990, 42.
30. W. Fuchs, Monatsh. Chem., 1915, 36, 113.
31. G. A. Kubiczak, F. Oesch, J. T. Borlakoglu, H. Kunz, and L. W. Robertson, J. Agric. Food Chem., 1989, 37, 1160.
32. C. van de Bunt, Recl Trav. Chim. Pays-Bas, 1929, 48, 121.
33. G. B. Deacon and G. J. Farquharson, Aust. J. Chem., 1976, 29, 627.